[(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2S)-2-ethyl-7-phenylmethoxy-3,4-dihydrochromene-2-carboxylate | 406488-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2S)-2-ethyl-7-phenylmethoxy-3,4-dihydrochromene-2-carboxylate
• CAS: 406488-85-5
• 化学式: C₂₅H₂₈O₆
• 分子量: 424.494
• InChiKey: TXGVMEFXQKMTJT-OFVILXPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2S)-2-ethyl-7-phenylmethoxy-3,4-dihydrochromene-2-carboxylate 在 sodium hydroxide 、 氢气 、 caesium carbonate 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 65.0~70.0 ℃ 、344.74 kPa 条件下， 反应 5.0h， 生成 (2S)-7-(3-(2-Chloro-4-phenoxyphenoxy)propoxy)-2-ethylchromane-2-carboxylic acid
  参考文献：
  名称：

  (2R)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents

  摘要：

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-{3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.

  DOI：

  10.1021/jm030621d
• 作为产物：
  描述：

  ethyl 7-hydroxychromane-2-carboxylate 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium hexamethyldisilazane 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 、 丙酮 为溶剂， 反应 61.0h， 生成 [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (2S)-2-ethyl-7-phenylmethoxy-3,4-dihydrochromene-2-carboxylate
  参考文献：
  名称：

  (2R)-2-Ethylchromane-2-carboxylic Acids:  Discovery of Novel PPARα/γ Dual Agonists as Antihyperglycemic and Hypolipidemic Agents

  摘要：

  A series of chromane-2-carboxylic acid derivatives was synthesized and evaluated for PPAR agonist activities. A structure-activity relationship was developed toward PPARalpha/gamma dual agonism. As a result, (2R)-7-{3-[2-chloro-4-(4-fluorophenoxy)phenoxy]propoxy}-2-ethylchromane-2-carboxylic acid (48) was identified as a potent, structurally novel, selective PPARalpha/gamma dual agonist. Compound 48 exhibited substantial antihyperglycemic and hypolipidemic activities when orally administered in three different animal models: the db/db mouse type 2 diabetes model, a Syrian hamster lipid model, and a dog lipid model.

  DOI：

  10.1021/jm030621d